DE2916589A1 - Verfahren zur herstellung von terephthalsaeure - Google Patents
Verfahren zur herstellung von terephthalsaeureInfo
- Publication number
- DE2916589A1 DE2916589A1 DE19792916589 DE2916589A DE2916589A1 DE 2916589 A1 DE2916589 A1 DE 2916589A1 DE 19792916589 DE19792916589 DE 19792916589 DE 2916589 A DE2916589 A DE 2916589A DE 2916589 A1 DE2916589 A1 DE 2916589A1
- Authority
- DE
- Germany
- Prior art keywords
- xylene
- reaction mixture
- acid
- terephthalic acid
- free
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 40
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 229910001882 dioxygen Inorganic materials 0.000 claims description 14
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052748 manganese Inorganic materials 0.000 claims description 12
- 239000011572 manganese Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- -1 aliphatic ketones Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 9
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000002696 manganese Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 150000002815 nickel Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Chemical class 0.000 description 2
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229940078494 nickel acetate Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89942578A | 1978-04-24 | 1978-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2916589A1 true DE2916589A1 (de) | 1979-10-31 |
Family
ID=25410944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792916589 Withdrawn DE2916589A1 (de) | 1978-04-24 | 1979-04-24 | Verfahren zur herstellung von terephthalsaeure |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE875728R (cs) |
| DE (1) | DE2916589A1 (cs) |
| FR (1) | FR2424248A2 (cs) |
| GB (1) | GB2019395B (cs) |
| IT (1) | IT1166769B (cs) |
| NL (1) | NL7903230A (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN152155B (cs) * | 1978-10-02 | 1983-11-05 | Labofina Sa | |
| EP0041785B1 (en) * | 1980-06-10 | 1985-05-02 | Imperial Chemical Industries Plc | Oxidation of substituted aromatic compounds to aromatic carboxylic acids |
| EP0041778B2 (en) * | 1980-06-10 | 1988-08-24 | Imperial Chemical Industries Plc | Oxidation of meta- or para-xylene to iso- or tere-phthalic acid |
| EP0041784A1 (en) * | 1980-06-10 | 1981-12-16 | Imperial Chemical Industries Plc | Oxidation of substituted aromatic compounds to aromatic carboxylic acids |
-
1979
- 1979-04-09 GB GB7912419A patent/GB2019395B/en not_active Expired
- 1979-04-20 BE BE0/194730A patent/BE875728R/xx not_active IP Right Cessation
- 1979-04-23 FR FR7910151A patent/FR2424248A2/fr active Granted
- 1979-04-24 IT IT22116/79A patent/IT1166769B/it active
- 1979-04-24 DE DE19792916589 patent/DE2916589A1/de not_active Withdrawn
- 1979-04-24 NL NL7903230A patent/NL7903230A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2019395A (en) | 1979-10-31 |
| FR2424248A2 (fr) | 1979-11-23 |
| IT1166769B (it) | 1987-05-06 |
| NL7903230A (nl) | 1979-10-26 |
| FR2424248B2 (cs) | 1984-01-20 |
| IT7922116A0 (it) | 1979-04-24 |
| GB2019395B (en) | 1982-07-28 |
| BE875728R (fr) | 1979-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |